$130 Find Cheap Flights from Greenville to Caribbean Islands - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Greenville to Caribbean Islands departing on 8/18. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Cheap Flights from Greenville to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$523
Santo Domingo
Santo Domingo1 stop$550
Montego Bay
Montego Bay1 stop$392
Oranjestad
Oranjestad1 stop$590
Nassau
Nassau1 stop$446
Kingston
Kingston1 stop$734
Simpson Bay
Simpson Bay1 stop$535
Providenciales
Providenciales1 stop$769
Port of Spain
Port of Spain1 stop$560
George Town
George Town2 stops$597
Willemstad
Willemstad1 stop$669
Aguadilla
Aguadilla1 stop$386
St. John's
St. John's1 stop$799
Punta Cana
Punta Cana1 stop$523
Santo Domingo
Santo Domingo1 stop$550
Montego Bay
Montego Bay1 stop$392
Oranjestad
Oranjestad1 stop$590
Nassau
Nassau1 stop$446
Kingston
Kingston1 stop$734
Simpson Bay
Simpson Bay1 stop$535
Providenciales
Providenciales1 stop$769
Port of Spain
Port of Spain1 stop$560
George Town
George Town2 stops$597
Willemstad
Willemstad1 stop$669
Aguadilla
Aguadilla1 stop$386
St. John's
St. John's1 stop$799

Book Cheap Greenville to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Greenville to Caribbean Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Greenville to Caribbean Islands

Mon, Aug 17 - Thu, Aug 20
Multiple Airlines Logo
3:13 pm - 12:41 am
GSP
-
SJU
9h 28m
1 stop
Multiple Airlines Logo
5:15 pm - 7:33 pm
SJU
-
GSP
26h 18m
1 stop
$253Multiple Airlines
Fri, Sep 11 - Tue, Sep 15
Multiple Airlines Logo
6:03 pm - 11:57 pm
GSP
-
SJU
5h 54m
1 stop
Multiple Airlines Logo
4:39 pm - 7:44 pm
SJU
-
GSP
27h 05m
1 stop
$266Multiple Airlines
Thu, Aug 20 - Thu, Aug 27
Multiple Airlines Logo
8:37 am - 4:11 pm
GSP
-
SJU
7h 34m
1 stop
Multiple Airlines Logo
5:15 pm - 7:33 pm
SJU
-
GSP
26h 18m
1 stop
$270Multiple Airlines
Fri, Aug 28 - Mon, Aug 31
Multiple Airlines Logo
6:41 pm - 4:11 pm
GSP
-
SJU
21h 30m
1 stop
Multiple Airlines Logo
6:35 am - 4:44 pm
SJU
-
GSP
10h 09m
1 stop
$274Multiple Airlines
Fri, Sep 25 - Sun, Sep 27
Multiple Airlines Logo
2:18 pm - 11:38 pm
GSP
-
SJU
9h 20m
1 stop
Multiple Airlines Logo
5:12 pm - 2:28 pm
SJU
-
GSP
21h 16m
1 stop
$276Multiple Airlines
Fri, Oct 30 - Wed, Nov 4
Delta Logo
7:45 am - 12:07 pm
GSP
-
MBJ
5h 22m
1 stop
Delta Logo
2:32 pm - 11:37 pm
MBJ
-
GSP
9h 05m
1 stop
$392Delta
Fri, Oct 30 - Wed, Nov 4
American Airlines Logo
8:31 pm - 11:12 am
GSP
-
MBJ
15h 41m
2 stops
American Airlines Logo
11:05 am - 9:50 pm
MBJ
-
GSP
10h 45m
1 stop
$397American Airlines
Sun, Aug 23 - Sat, Aug 29
American Airlines Logo
7:00 am - 4:08 pm
GSP
-
MBJ
10h 08m
1 stop
American Airlines Logo
3:23 pm - 10:24 am
MBJ
-
GSP
18h 01m
1 stop
$399American Airlines
Wed, Nov 18 - Wed, Nov 25
Delta Logo
6:45 am - 2:40 pm
GSP
-
SDQ
6h 55m
1 stop
Delta Logo
3:55 pm - 9:21 pm
SDQ
-
GSP
6h 26m
1 stop
$550Delta
Sat, Jan 16 - Sat, Jan 23
United Airlines Logo
6:00 am - 2:20 pm
GSP
-
STX
7h 20m
1 stop
United Airlines Logo
3:25 pm - 11:19 pm
STX
-
GSP
8h 54m
1 stop
$564United Airlines
Booking Insights

KAYAK's insights & trends for Greenville to Caribbean Islands flights

Get data-powered insights and trends into flights from Greenville to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Greenville to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $359, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Greenville to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Greenville to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Greenville to Caribbean Islands is September, when tickets cost $531 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $776 and $761 respectively.

How far in advance should I book a flight from Greenville to Caribbean Islands?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Greenville to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Greenville to Caribbean Islands, you should book around 6 weeks before departure, which saves you about 15% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Good to know

Low season

August

Cheapest flight

$130
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly with an average 17% increase in price.
Flight from Greenville to San Juan

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Greenville to Caribbean Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Greenville to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Greenville to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Greenville to Caribbean Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Greenville to Caribbean Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Greenville to Caribbean Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Greenville to Caribbean Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Greenville to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Greenville to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Greenville to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Greenville to Caribbean Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.8
DeltaOverall score based on 8479 reviews
7.2Food
8.5Crew
8.1Boarding
7.8Comfort
7.8Entertainment
Airline reviews

This flight was originally delayed by ~45 minutes; which is fine. However, there were additional delays due to late offboarding of the prior flight, unclear issues with the boarding process, delays on the tarmac, and exceptionally long taxiing. None of these issues were communicated proactively. Additionally, the flight had exceptionally rough turbulence, which led to a very uncomfortable flight and no traditional beverage service. Again, this is understandable, but it was not communicated up-front by the flight team.

2.0 MediocreAidan, Jul 2026
RDU - BOS
Read more Delta reviews

This flight was originally delayed by ~45 minutes; which is fine. However, there were additional delays due to late offboarding of the prior flight, unclear issues with the boarding process, delays on the tarmac, and exceptionally long taxiing. None of these issues were communicated proactively. Additionally, the flight had exceptionally rough turbulence, which led to a very uncomfortable flight and no traditional beverage service. Again, this is understandable, but it was not communicated up-front by the flight team.

My flight was canceled, and instead of rebooking me on a non-stop first-class flight for the same day, which I originally had, Delta rebooked me on a one-stop flight for the following day. When I checked the Delta app, I noticed that there were available flights for both the same day and the next day. I believe this indicates poor management on their part.

The Columbus-based WestJet crews that cover Delta commuter flights between LGA and CMH are excellent - this team included. Our flight today landed 40 minutes early, which is unheard of when flying out of LaGuardia. I've flown with the same crew in more challenging conditions, and they always rise to the occasion with helpful communication to the passengers so that we may manage expectations.

This wasn't my experience with Delta. It was just the Pegasus flight. Seats were very hard. Staff was kinda rough. Not very nice. Charged me for snacks. For a 4 hour flight I would've expected more.

I had a flight cancel and had it rerouted. When the rerouted they put me at a window seat instead of an isle. It was hard sitting by the window because the couple with masks on were making out. I get motion sickness which is why I need to have the isle seat.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

I just can’t understand why are you sell to many tickets ???? We had to wait 2 hours before 13 people from our flight take money and go to next day flight!

The only real hiccups in the flight were things beyond Delta’s control - turbulence which delayed food service and a departure delay caused by some VIP plane which stopped all departures and landings for 30 minutes - and was never explained to us by the crew. Otherwise good flight. I would fly Delta again.

The plane was frigid, and leaked water from the ceiling all over me and my seat.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

Flight was fine, but not having WiFi was a major negative

Everything was excellent and I enjoyed myself. Thank for everything

One of our group members was struggling to walk. In Charlotte we asked for a wheelchair and she was accompanied by Desmond. I was impressed by his patience and attention. In Boston she received the same service. I didn’t get the name of the helper but she went above and beyond in assisting us. A great AA service

I was trying to take 2 one and a half hour one way trips and I experienced almost 20 delays over the course of those two trips. Only a few of them were due to weather the rest was disorganization

Would have thought that they would gas up plane before everyone got on board

The flights were terribly delayed and then cancelled which forced us booking another night at the hotel. Very poor management from American Airlines

When my flight was delayed due to weather, I was rebooked to another flight since it showed that I would miss my connection. It was a lot of work to get back onto my originally connecting flight which was also delayed. That part caused a lot of stress and frustration. The ticketing agent at the desk was not very helpful.

American switched my flight to a 5 hour layover then cancelled my whole reservation with no notice and refused refund. Won’t fly with them again.

We sat on runway for an 1 hour because they were short handed at key west airport was not fun

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports